One-Pot Tandem Synthesis of Nitriles and Amides from Biomass Platform Compounds

Abstract

In recent years, research on converting biomass platform compounds into high-value chemicals and pharmaceutical intermediates has garnered huge interest. Nitrile and amide groups are key structures in natural products and biologically active molecules. The direct conversion of biomass platform compounds into nitriles and amides will undoubtedly be an important guide for biomass utilization. In this paper, a facile and efficient triphosgene-assisted one-pot conversion for aldehydes and ketones into nitrile and amides is presented. Triphosgene is a phosgene alternative that contains both ester linkage and chloromethyl units and easily reacts with oximes for the preparation of nitriles and amides. However, due to the hydrolysis of oximes to aldehydes or ketones, the reaction of oximes with triphosgene cannot fully convert the corresponding nitriles and amides. The protocol tandem ensures a smooth process without the use of organic bases or metal catalysts. Using biomass-derived platform compounds, various functionalized aromatic, aliphatic, and allylic aldehydes and ketones were successfully converted to nitriles and amides in excellent yields. In comparison to step-by-step reactions, this tandem strategy features multi-step reactions in one pot, mild reaction conditions, and fewer by-products.